Methyl 2-methoxy-3-nitrobenzoate → Methyl 3-amino-2-methoxybenzoate

HRID 1671014Notes

Reaction equation

HRID 1671014 reaction equation
[CH3:1][O:2][C:3]1[C:12]([N+:13]([O-])=O)=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]>CO.[Ni]>[NH2:13][C:12]1[C:3]([O:2][CH3:1])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 1

HCID 590805Methyl 2-methoxy-3-nitrobenzoate

Product 1

HCID 13338715Methyl 3-amino-2-methoxybenzoateYield 96.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 2-methoxy-3-nitrobenzoate (28.4 g, 134 mmol) in MeOH (150 mL) was added Raney Ni (3 g). The mixture was stirred under H2 atmosphere (50 psi/25 IC) for 3.5 h. The catalyst was filtered, and the filtrate was concentrated under the reduced pressure to dryness to give the crude product, which was purified by recrystallization in EtOAc to afford the title compound of Step C, methyl 3-amino-2-methoxybenzoate (23.5 g, 96.4% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 6.80-6.93 (m, 3H), 5.10-5.25 (br, 2H), 3.78 (s, 3H), 3.67 (s, 3H).

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate was concentrated under the reduced pressure to dryness
  3. customto give the crude product, which
  4. customwas purified by recrystallization in EtOAc

Sources & evidence

ORD record
ord-cfb29c72ac254058ad7de4fa23046b18
Source dataset
uspto-grants-2011_08
Patent number
US07994185B2

Reaction notes

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